Startup Therapy

Hosted by Startups.com

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Episodes

336

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Jun 2026

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About the show

The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.

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June 15, 2026Episode 33633 min

Founders Don't Retire

What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: founders are wired to create, not to consume, and the fantasy of beach life usually shows up at a low-energy point when what’s really needed is recovery. They compare founder burnout to wanting the finish line without running the race, and note how exits often lead from “margaritas” to “domain names” within months because the calling returns once the nervous system resets. The key reframe: separate a recovery plan from a retirement plan, and define “retirement” as creating on your own terms—less panic, fewer hated parts (like investor pressure or endless hours), more control, and a sustainable way to keep doing the work you love.What to listen for:00:49 Builder DNA and Relief00:57 Carpenter Story and Pain03:06 Four Minute Founder Brain04:31 Broken Retirement Dream05:13 Reload and Retire Again06:31 Beach Metaphor Explained09:58 Athletes vs Founder Longevity12:00 Vacation Checklist Trap15:35 No Substitute for Mission17:29 Finish Line Fantasy18:45 Recovery Not Retirement20:35 Builders Need Purpose25:14 Retired But Uncharged27:00 Creation Over Consumption30:16 Retirement On Your Terms32:26 Design Better CircuitsResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

June 8, 2026Episode 33538 min

The Right Time to Start is Right Now

Ever feel like you’re “almost ready” to launch—just one more feature, plan, or credential away? This episode argues that “ready” isn’t a prerequisite for startups; it’s the result of starting and getting real market feedback. Using examples like selling early software for $1,500, learning web building on the fly, a disastrous (but educational) client pitch moment, and even an impulsive scuba dive, the discussion shows why planning can become productive-looking theater when nothing is being tested. The real cost of waiting isn’t just lost time—it’s lost learning, missed customers, and negative compounding versus competitors who take action. Planning has value only when it directly leads to action, because failure and iteration are the mechanism that reveals what works.What to listen for:01:14 Plans Meet Reality02:00 Readiness Comes After02:34 First Founder Breakthrough07:41 Micro Center Origin Story10:07 Cost of Waiting11:14 Planning Versus Theater12:23 Test With Customers14:09 Ecommerce Pitch Fail16:41 Whiteboard Versus Field18:48 Learning By Building19:35 Learn By Doing20:05 Founder Skill Stack20:45 Econ 101 Mindset Shift22:45 Human Potential Unlocks24:27 Momentum Beats Certainty25:58 Plan To Learn Fast30:26 Conditioned To Avoid Failure34:34 Cost Of Waiting35:50 Action Over Perfection36:47 Stop Waiting Start NowResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

June 1, 2026Episode 33446 min

The Most Expensive Equity Doesn't go to Investors

Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade because cash and terms are clear, while “everyone else pays in maybes and promises.” It warns that early-stage equity feels worthless but represents 100% of a company’s future value, so giving away 50% to a near-stranger can become a permanent cap table problem that also costs speed, optionality, and sanity. Practical fixes include vesting, cliffs, tying equity to real value creation, defining what happens if someone stops contributing, and putting breakup terms in writing early. The discussion also critiques employee equity as time-based rather than performance-based, and advisor equity as often unaccountable, where tiny percentages can hide very expensive outcomes.What to listen for:00:00 Investor vs Founder Equity01:26 Equity Is Priceless03:43 Co-Founder Split Hangover06:04 Why People Underperform11:15 Fairness Turns To Resentment12:44 Will's Unsubscribe Story15:53 Vesting And Breakup Terms18:17 Early Employees Option Pool20:26 Equity As Compensation Trade21:59 Paying Twice With Equity22:14 Does Equity Change Effort23:10 Lottery Ticket Reality27:23 Equity Rewards Three Things27:37 Advisor Equity Math31:00 Reputation Versus Contribution33:30 Network Intros Social Capital35:56 Advice Has Shelf Life40:24 Pricing Advisor Time44:06 Treat Shares Like CashResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

May 25, 2026Episode 33335 min

How to be Great at Worrying

Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant vigilance can turn into fear dressed up as responsibility—endless rumination that produces stress, not decisions. Will shares decades of 3:00 AM worry cycles, the superstition that anxiety prevents disaster, and how even vacations get hijacked by disaster simulations (including getting hacked on the way to Comic-Con). They draw a line between real thinking that creates options and looping that creates suffering, then discuss practical replacements: box breathing to fall back asleep, gratitude to reset perspective, and self-talk that puts the “experienced founder” back in charge. The goal isn’t to stop worrying, but to channel that energy into small, solvable actions instead of spirals.What to listen for:00:41 Learning to Worry01:21 Walk the Lot Mindset03:28 Fear as Responsibility05:07 Paranoia and 3AM Ceilings06:25 Anxiety Superstition Loop08:18 Vacation Disaster Mode10:21 Thinking vs Rumination13:10 Breathwork Replacement14:14 Milestones Won't Fix It15:53 Experience Adds Knives18:47 Fear Makes It Worse19:39 Worry As Energy21:24 Productive Distractions22:29 Finish Small Tasks23:39 Save It For Morning27:17 Worry Versus Solving31:13 One Pebble At A Time34:59 Make Worry A SuperpowerResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

May 18, 2026Episode 33243 min

Can Startups Be a Team of One?

What happens if building a startup no longer requires a team? The conversation explores how AI is rapidly turning the classic “product + developer + marketer” founding trio into an optional choice, making one-person companies the new default as tools get dramatically better and far cheaper than hiring. They unpack how this shift changes equity, speed, and the quality filter that co-founders and teams used to provide, while also threatening many “on-ramp” roles like customer support and other knowledge-based services (accounting, payroll, legal). They wrestle with the economics that push founders toward AI, the competitive pressure that makes it feel unavoidable, and the human costs—loneliness, loss of pushback, and erosion of culture. Ultimately, they argue that hiring humans may become a luxury reserved for uniquely human value: creativity, leadership, intuition, and genuine connection.What to listen for:01:04 Inside View of Founders02:38 Economics Meets Capability03:01 Generational Shift in Startups05:58 From Co-Founders to AI09:09 Equity as Quality Filter10:44 Humans Optional Now12:04 One Person Startup Math14:23 Moats Erode Overnight15:32 Jobs First to Disappear18:14 Disruption and New Demand19:59 Next Roles on the Chopping Block21:00 Gatekept Knowledge Flips22:01 AI Becomes Hygiene23:45 Where Humans Matter24:33 Pushback And Refinement28:33 Loneliness Rubber Band30:36 Humans As Luxury34:20 Hiring Math Breaks39:02 Culture Versus CostResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

May 11, 2026Episode 33133 min

Why are we Really Building a Startup

What are you really trying to fix by building this company—and what happens when you finally admit it? The conversation unpacks how founders often default to a public “change the world” story while their private motive is something more personal like safety, control, validation, belonging, autonomy, or even revenge. When that real why stays hidden, decisions get miscalibrated and founders chase the hardest possible path (like massive VC rounds) even when a smaller outcome might satisfy the true need. They discuss how these motives “leak out,” especially after selling a company and realizing you’re no longer needed, and why success (even IPO-level) rarely erases old wounds. The key is naming the motive, right-sizing the plan to it (“minimum viable ego”), and building a deliberate version of success that fits what you’re actually optimizing for.00:00 Founders Lie to Themselves01:53 Public Why vs Private Motive02:58 Freudian Roots of Drive03:37 Will’s Safety and Control Story07:11 When the Why Leaks Out07:35 Selling and Not Being Needed09:57 Validation as True North12:01 Ryan’s North Star Revealed13:45 Will’s Revenge and Proving16:07 Steve Jobs Still Hurt17:57 Haters And Criticism18:44 Minimum Viable Ego19:29 Different Success Thresholds20:47 Stop Trying To Prove Them21:22 Pick The Right Vehicle22:05 The Villain You Invent23:45 Success Doesnt Fix You29:17 Money And Marriage Myths30:25 Alignment Over Ego Death31:03 Autonomy As The Real Goal32:34 Own Your MotivationResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

April 14, 2026Episode 33046 min

We Rarely "Control" Our Startups

Worried about “losing control” because of dilution? This episode breaks down why equity is a poor proxy for control in startups: the cap table splits money, while control is defined by decision rights in the operating agreement and enforced through board voting. The hosts explain how founders can own most of the company yet still need permission for key actions (like senior hires), how boards are built (often 2 founders, 2 investors, 1 independent), and how board math can outweigh founder ownership—especially when things go wrong. They also cover how operating agreements get rewritten each funding round, how founders can be fired even if they own a majority, and why investors can control outcomes through financial leverage when runway is low. The core advice: define non-negotiables early, focus on governance and runway, and stay funded and credible.What to listen for:00:00 Control Is Not Equity00:29 Investor Leverage Wake Up Call02:53 What Founders Mean By Control04:08 Co Founder Control Myth07:47 Operating Agreement Rules10:57 Protective Provisions Explained14:48 You Can Be Fired19:07 Boards And Governance21:47 How Funding Changes Control24:13 Board Coup Reality24:42 Board Math Wins25:25 Voting vs Ownership26:32 Operating Agreement Changes28:52 Cash Leverage Control32:27 Credibility and Sentiment35:46 Founder Nonnegotiables40:43 Change of Control Rights44:00 Exit and Liquidity Traps45:19 Governance Over EquityResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

April 6, 2026Episode 32938 min

Founders Need Finish Lines

Ever feel like you hit a milestone in your startup and immediately get handed the next problem? The episode explores why startup work rarely delivers a true sense of “done,” how founders get trapped by the arrival fallacy (believing the next round, milestone, or cushion will finally bring relief), and how the constant threat of being “eaten” by faster competitors turns ambition into paranoia. Ryan and Will compare the endless nature of startups to more finite work, discuss how chasing metrics and despising complacency fuels chronic restlessness, and share personal examples of goals that didn’t bring fulfillment. Their takeaway: startups are an infinite game, so founders need to create completion outside work—through finishable, tangible activities like cooking, workouts, sports, cleaning, or building projects—because completion is psychological maintenance, not a luxury.What to listen for:01:37 Goals vs Fulfillment02:46 Arrival Fallacy Explained03:42 Milestones Aren't Meaning05:16 Dopamine and Restlessness05:40 Painful Arrivals Stories09:13 Despising Complacency11:00 Getting Eaten Alive by Change16:09 Contentment vs Career Metrics18:24 Ad Break and Lamborghini Setup19:22 Breaking Down The Fees19:40 Paranoia About Losing It20:30 Advice Comes With Bias21:08 Founder Scarcity Mindset22:54 Finding Completion Offline26:32 Why Startup Wins Feel Empty31:41 Small Finishes Refill The Tank33:16 Buying Stuff Won’t Fix It35:57 Appreciation Versus Earning37:34 Manufacture Your Finish LineResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

March 23, 2026Episode 32847 min

What Should My Expectations Be?

Ever feel like you’re working nonstop and still falling behind? The discussion argues founder happiness and decision-making improve fastest by recalibrating expectations, because “happiness = reality ÷ expectations.” Using stories from trading work for pizza or restaurant tabs to later winning massive business, it highlights how low expectations can make progress feel rewarding, while the “snowflake myth” and unpriced optimism create entitlement and disappointment. They distinguish aspiration (what you’d like) from expectation (what must happen), urging founders to replace unicorn fantasies with concrete, earned milestones like revenue, payroll, and product-market fit. They stress startups take far longer than most timelines claim—often 5–10+ years—even for legendary companies, and warn that funding timelines and social comparison can trigger panic and bad decisions.00:37 Pizza Paper Hustle01:41 Rib Money Origins03:07 From Ribs to Lilly04:30 Happiness Math Formula05:59 Lambo Expectations Check07:47 The Snowflake Myth08:09 Optimism vs Expectation09:19 IPO Odds Reality10:53 Aspiration Not Debt12:07 Milestones Over Unicorns15:06 Time Myths and 3x Rule17:36 Funding Clocks and Panic20:42 Startup Mythology Trap24:08 Five to Ten Year Truth24:38 Overnight Success Myth25:19 Funding Timeline Trap26:01 Check Your Premises26:54 Entitlement Mindset28:19 Effort Versus Results30:05 Earning Versus Inheriting35:51 Milestones Not Home Runs37:57 Small Wins Ladder41:06 Expectations And ComparisonResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/

March 2, 2026Episode 32734 min

What Actually Happens When A Founder Runs Out of Gas?

What do you think really happens if you burn out and step away for a minute? The conversation breaks down how founders often imagine an apocalyptic chain reaction—customers leaving, the team collapsing, investors panicking—when in reality burnout is a predictable capacity ceiling and most worst-case scenarios don’t happen. They argue the real danger is pretending burnout won’t come, pushing until physical failure, and keeping recovery secret, which can create the chaos founders fear. Using sports analogies, they emphasize that staying “on the field” nonstop makes you a liability, and that planned breaks build resilience, give teams room to step up, and help founders regain creativity and effectiveness. The core takeaway: treat recovery like required maintenance, plan for it, and build a company that doesn’t depend on you 24/7.What to listen for:00:57 Apocalypse Scenario02:12 Always On Mentality03:49 No Built In Breaks06:56 Superman Plan Fails08:06 Burnout Warning Signs10:32 Atlas Shrugged Reality15:22 Hockey Shift Lesson16:23 Fear of Replacing Yourself16:46 Stop Guessing Get Help17:19 Burnout Nightmare Myths19:14 When Investors Shrug20:57 Youre Not The Main Character23:24 Let The Team Step Up25:14 Breaks Prevent The Crash27:06 Vacation ROI Mindset29:34 Plan Recovery Like Taxes31:44 Durable Not Tireless33:22 No Great Company Empty TankResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/